3-Bromobenzonitrile → 3-pyrrolidin-1-ylbenzonitrile

HRID 1167301노트

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HRID 1167301 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[NH:62]1[CH2:66][CH2:65][CH2:64][CH2:63]1>O1CCCC1.C(OCC)C.O>[N:62]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH2:66][CH2:65][CH2:64][CH2:63]1

참가 물질

8

반응물 4

HCID 233813-BromobenzonitrileHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

생성물 1

HCID 71623323-pyrrolidin-1-ylbenzonitrile수율 5.2%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A reaction mixture of 3-bromo-benzonitrile (0.91 g, 5 mmol), tris(dibenzylidenecetone)-dipalladium (229 mg), (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (311 mg, 0.5 mmol), sodium tert-butoxide (740 mg, 7.7 mmol), pyrrolidine (0.58 mL, 6.9 mmol) in tetrahydrofuran (10 mL) was heated at 80° C. in a sealed tube for 6 h. The reaction mixture was worked up with water and diethyl ether. The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% ethyl acetate in hexanes yielded 3-pyrrolidin-1-yl-benzonitrile (45 mg, 5%).

후처리

  1. washThe organic layers were washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe solid was then filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  6. washeluting with 0-5% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-50de50b618b444b6936f0c49cef43f12
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617346B1

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